We were lucky to catch up with Amanda Caswell recently and have shared our conversation below.
Hi Amanda, thank you for being such a positive, uplifting person. We’ve noticed that so many of the successful folks we’ve had the good fortune of connecting with have high levels of optimism and so we’d love to hear about your optimism and where you think it comes from.
The simplest answer would be, my optimism comes from my mother. She is one of those radiant, joyful people who makes friends wherever she goes, including while waiting in the grocery store lineup. It frustrated me to no end growing up, because everything took so much longer than I wanted it to. But I see now what a gift it is and appreciate how it has permeated the way I navigate the world. Her delight in other people and her insistence on connecting with their humanness can make all the difference to someone feeling like they belong, that they matter. Everyone has things they carry that no one else can see, and I truly do believe that ultimately people want the same things as everyone else — love, connection, belonging, safety. We just have different (and sometimes conflicting) ideas on how best to achieve that. A friend of mine once likened me to this phrase that is from an old Jewish tradition, that of turning the gem. Of holding scripture like a precious stone up to the light and seeing how, like a prism, it reflects back different perspectives. My inclination is to step out of my own initial experience of something and to see it from other vantage points. This has been such a helpful skill in my work as a strategist, to envision many possible outcomes and facets to explore. As I have been developing my skills in mindfulness and integration, I also feel I now have more ability to stay with my own instinctive experience and not deflect out to the broader picture or alternative interpretations. Both/and can be true. There is always another possibility available, if we can be with the discomfort of the unknown.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
My career is in a period of shapeshifting, so there are many possible answers to that question. The most straightforward of the answers is that I work in naming and identity strategy. That means I help leaders of brands and organizations clarify what they value and express it in ways that resonate with their intended audiences. Though it might look like being a copywriter, I’m working at the stage before that — the stage where what this thing even IS is still being defined. My clients tend to be technical geniuses that are communicating a lot of complexity or adding in more of the emotional context that guides how people choose their services. Much of my work is in B2B industries like tech, healthcare, engineering, finance and professional services, like coaching or law, but sometimes I work in consumer products too, like snack foods or beauty.
My favourite kinds of projects are the ones where we are closing the gap between what my clients aspire to be and how they make it real, like defining values or purpose in service of client experiences and culture change. These strategic words, that leaders spend so much time fine-tuning, often end up inert in powerpoint purgatory or dusty as posters on the wall. Your values should be living breathing things, that inspire new ideas and help guide your decision-making. When you get to work with leaders that see the value of language in clarifying where they want to go and equipping folks with what they need to get there, it’s like weaving a magic spell to create more alignment, traction and meaning.
My consulting practice is mainly known for naming, which as a project type, reflects the inflection point between a lot of different disciplines — strategy, R&D, marketing and legal. We need to get all those folks on the same page, about what kind of product this is and how best to position it. A lot can go wrong, and usually by the time folks have reached a specialist like me, they’ve had their ideal name (or many) fail the registration process. Naming is very subjective and often business pressures are driving a tight timeline, so the strategy gets skipped and the whole process ends up taking way longer. Working on a naming project requires being in an uncertain place for a sustained period of time, which can be really uncomfortable for business leaders who are juggling too many priorities at once.
Working in uncertainty led me to become a certified Integral Coach though New Ventures West a few years ago, which has been such a beautiful process of letting my career trajectory be changed by being more of the person I am, not by performing the person it has been valuable for me to be. Integral coaching is interested in letting people’s aliveness lead, by bringing their mind, body and spirit into alignment. When I was working strictly in marketing, I never felt lit up by what I was doing. Now, I see so many more opportunities for growth and learning that delight me and frankly, scare the shit out of me (a good sign!). I am studying mindfulness, somatics, parts work, tarot and astrology. I am working with things that feel taboo to an overculture that values certainty, perfectionism and shame as tools of control.
I want to bring expressive practices to people who do not think of themselves as creative. I want to help people build more self-trust through curiosity and self-compassion. When people come to questions of meaning and purpose, it is often because something is breaking down and has become painful. I like to bring more mystery, warmth and play into the mix. This feels as true of my work with individuals as it does for my work with organizations — I am working in service of <i>their</i> unique expression and self-concept, not my own.
So, in addition to my naming and brand practice, I host a free monthly drop-in Journal Circle that explores what is emerging in your experience through gentle, joyful prompts and poetry. I offer 1:1 coaching and tarot readings. I am probably a good person to talk to if you say “yes” too often and struggle to slow down. I haven’t found a short way to talk about all of these disparate threads yet, but just give me time 😉
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
To work in naming and the verbal side of brand identity, you have to be sensitive to nuances in language. I have always been a voracious reader and that has honed my sense of what words best suit the situation and tone. Read books. Read poetry. Read things offscreen sometimes. Read anything that interests you. Read “silly” stuff, like romance and sci-fi, that gives you the momentum to keep reading. Don’t only read things you feel like you “should” read, like business and science books. Fiction is an important part of your education too. Give your imagination a wide palette to draw from.
Honestly, if you’re ever planning on becoming self-employed, your network will be your most important business asset. Make friends with folks you work with and stay in touch, even if it’s sporadically. Be kind and generous with your time. Find people you can stumble over your words with and learn alongside. Join communities of people who want to learn what you want to learn, and ask to have coffee dates. Ask people what their work is like, what their life is like — people love talking about themselves and they are endlessly interesting if you slow down and become present to what they’re saying (and what they’re not saying).
The other thing that has helped me, and maybe this sounds weird, but I am not driven by the things that drive many other folks. I am not driven by money or fame. When I worked in advertising at the beginning of my career, all of the agencies I interviewed at just wanted to win awards. I always found when I worked on projects angling for awards, we lost sight of solving the clients’ real problems. I don’t care about applause, I just want to do good work. I want my clients to feel like I was there for them and what they are figuring out, not for how others might perceive my contribution. It means I’ve been able to work with many types of clients in many types of fields. It means I get to let my endless curiosity feel satisfied because I’m not locked into solving one kind of problem in one kind of way. It means I have a lot of flexibility in what my work life looks like at any given time, because my definition of success is not based on external validation. It means I trust what is enough, for myself, on my own terms, which feels like freedom.
What do you do when you feel overwhelmed? Any advice or strategies?
Being self-employed is a surefire path to come up against every last one of your triggers and growth edges. I generate a lot of ideas and I’m very curious about the world and other people, which means I’m often living far beyond the confines of my body and what is here and now. I help my clients define their visions, which means my ability to go really far out there, in a lot of directions, is a super valuable skill, but I can’t LIVE there. So that’s my first piece of advice — get rightsized again. Get back into your body, get back into what is close at hand, get back into your physical space. I am very grateful to have had good teachers who have led me to practices that help me become bodysized again.
My favourite practice, so simple, is to feel your back. If you are sitting, let your bum become heavy, and feel the small of your back press back into the chair. Take a couple breaths and direct them to those points of contact, holding you up. You are here, now, not wherever your mind has been spinning off. We humans get very confused about this, understandably. The only work it is possible to do is right here and now. We can know this logically, but being in practice with it, of experiencing it over and over, it begins to change you. This is true for anything you envision — you need to come back to your body here and now. You can let the vision influence how it is possible to show up in your current circumstances, but you can’t begin from the ether of a future that doesn’t exist.
The other piece of advice I have is to get it out of your head and out of your body. There is a great quote from David Allen, “Your brain is for having ideas, not storing them.” It’s much easier to get stuck in the mental swirl if I’m not writing regularly, especially writing by hand. It is helpful to slow my thoughts down to the pace of my hand, even if I get impatient with it. When I am in a regular notetaking process, everything else seems to flow with more ease. I will also say, we are taught to be very still as civilized grownups. Move your body, shake it out, especially if you’re experiencing something stressful or activating. We are animals, after all, though we might forget. It doesn’t have to be a big deal — just shake out your hands, or put on music and dance, maybe do some arm circles, roll out your neck. Give yourself a chance to MOVE so the overwhelm doesn’t get stuck and calcified within you.
Contact Info:
- Website: amandacaswell.com
- Instagram: https://www.instagram.com/_amandacaswell_/
- Linkedin: https://www.linkedin.com/in/amandacaswell/
- Other: Bluesky: https://bsky.app/profile/amandacaswell.com Threads: https://www.threads.net/@_amandacaswell_?hl=en

Image Credits
Stephanie Pellett
